Dimethylformamide → 8-Chloro-9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 221984Notes

Reaction equation

[C:1]1([C:7]2[C:8](=O)[NH:9][C:10]3[CH:11]=[CH:12][N:13]4[C:19]([C:20]5[N:25]=[CH:24][CH:23]=[CH:22][N:21]=5)=[N:18][N:17]=[C:14]4[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:34]>C(#N)C>[Cl:34][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][C:15]2[C:14]3=[N:17][N:18]=[C:19]([C:20]4[N:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:13]3[CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one (2-4) (1.4 g, 4.1 mmol) and DMF (0.032 mL) in acetonitrile (20 mL) was added POCl3 (2.3 mL, 24.6 mmol). After stirring at 120° C. for overnight, the solvent was removed under reduced pressure, and the residue was diluted with acetonitrile, and added water. The resulting solid was collected by filtration to give 8-chloro-9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine (2-5) as a colorless solid.

Workup

customthe solvent was removed under reduced pressure
additionthe residue was diluted with acetonitrile
additionadded water
filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-3bfd61dc9c3d4b24aecf64f1573baddb
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207169B2

Reaction notes

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